Dimethylamine → (S)-2-(4-Chlorophenyl)-N,N,alpha-trimethyl-3H-imidazo[4,5-b]pyridine-3-acetamide

A solution of (S)-2-(4-chlorophenyl)-α-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0166 mole), 1,1'-carbonyldiimidazole (3.21 g, 0.0198 mole) and dry tetrahydrofuran (100 ml) was stirred at room temperature for 3 hours with nitrogen bubbling through it. A solution of dimethylamine (2.26 g, 0.050 mole) in tetrahydrofuran (20 ml) was added and the reaction mixture was stirred at room temperature under nitrogen overnight. The mixture was evaporated to an oil and partitioned between ethyl acetate (50 ml) and water (50 ml). The layers were separated and the aqueous layer was re-extracted with ethyl acetate. The combined organic layers were washed once with water (50 ml), twice with 5% potassium hydroxide solution (50 ml portions), and once more with water (50 ml). Drying over magnesium sulfate, treatment with charcoal, filtration and evaporation of the solvents gave a residue which upon recrystallization from hot isopropyl ether and drying under high vacuum gave 3.20 g (59%) of title compound, mp 124°-126° C.

1. customThe mixture was evaporated to an oil
2. custompartitioned between ethyl acetate (50 ml) and water (50 ml)
3. customThe layers were separated
4. extractionthe aqueous layer was re-extracted with ethyl acetate
5. washThe combined organic layers were washed once with water (50 ml), twice with 5% potassium hydroxide solution (50 ml portions)
6. dry with materialDrying over magnesium sulfate, treatment with charcoal, filtration and evaporation of the solvents
7. customgave a residue which
8. customupon recrystallization from hot isopropyl ether
9. customdrying under high vacuum

ORD record

ord-34764cd0b12c470aa557810f7f2a0f94

Source dataset

uspto-grants-1990_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04948800